Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B57/00—Other synthetic dyes of known constitution
  • C09B57/04—Isoindoline dyes

Definitions

• the rings M in the formulas (VIIa) to (VIId) can also be substituted, for example by halogen, such as chlorine or bromine; Nitro, C 1 to C 6 alkyl and / or C 1 to C 6 alkoxy, preferably by chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
• halogen such as chlorine or bromine
• Nitro, C 1 to C 6 alkyl and / or C 1 to C 6 alkoxy preferably by chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
• divalent radicals -B- wherein the benzene and naphthalene rings are optionally substituted by halogen, such as chlorine or bromine, nitro, C 1 - to C 6 -alkyl and / or Ci- to Cs-alkoxy.
• halogen such as chlorine or bromine, nitro, C 1 - to C 6 -alkyl and / or Ci- to Cs-alkoxy.
• the rings are preferably unsubstituted or substituted by chlorine, bromine, methyl, ethyl, methoxy and / or ethoxy.
• Bis-isoindoline pigments of the formula (X) are particularly preferred in A 2 for identical or different radicals of the formulas and B 2 represents 1,4- or 1,3-phenylene which is optionally substituted by methyl, ethyl, methoxy, ethoxy, chlorine or bromine and in which R 8 is cyano, carbamoyl, N-methylcarbamoyl, N-ethylcarbamoyl or by chlorine, bromine, Methyl, methoxy or carbomethoxy substituted phenylcarbamoyl.
• bis-isoindoline pigments of the formula (XI) where R 9 is methyl or ethyl, R 10 is methyl, ethyl, methoxy, ethoxy or chlorine and n is 0, 1 or 2 and where n 2 the radicals R 10 may be the same or different.
• C 1 to C 4 alkyl are preferably to be mentioned in detail, for example: methyl, ethyl, n- and i-propyl, n- and i-butyl, butyl-2, tert-butyl. Pentyl, hexyl or 2,2-dimethylbutyl.
• C 1 - to C s -alkoxy C 1 to C 4 -alkoxy are preferred, for example: methoxy, ethoxy, n- and i-propoxy, n- and i-butoxy, pentoxy and hexoxy, of which Methoxy and ethoxy are particularly preferred.
• the compounds of the formula (I) can be prepared by stepwise reaction of compounds of the formula with diamines of the formula H 2 NB-NH 2 (XXIII) or, in the case of the radicals B of the formulas (VIIIq) and (VIIIr), by reaction with the hydrazides of the corresponding dicarboxylic acids with elimination of ammonia.
• the reactions are expediently carried out in inert organic solvents at temperatures from 20 to 150 ° C., preferably between 50 and 120 ° C.
• Suitable organic solvents are alcohols such as methanol, ethanol, amyl alcohol or glycol monoalkyl ether; Aromatics such as chlorobenzene, nitrobenzene or toluene; amidic solvents such as formamide, N, N-dimethylformamide or N-methylpyrrolidone; or acids such as formic acid or acetic acid.
• alcohols such as methanol, ethanol, amyl alcohol or glycol monoalkyl ether
• Aromatics such as chlorobenzene, nitrobenzene or toluene
• amidic solvents such as formamide, N, N-dimethylformamide or N-methylpyrrolidone
• acids such as formic acid or acetic acid.
• Aromatic hydrocarbons such as xylene, toluene, chlorobenzene or nitrobenzene or N, N-dimethylformamide can be used for the reactions with diisocyanates.
• Such asymmetrical compounds (I) can also by reacting a compound of formula (XII) with a nitroamino compound H 2 NB-N0 2 (XIIIa)
• the salts or complexes of the compounds of the formula (I) are prepared by processes known per se, for example by the compounds with the corresponding metal salts being in N, N-dimethylformamide, N-methylpyrrolidone or formamide for some time (approx. 5 to 10 h) heated to a higher temperature (approx. 140 ° C).
• the compounds of the formula (I) are obtained in a form suitable for pigment use or can be converted into the suitable form by post-treatment processes known per se, e.g. by grinding with or without grinding aids, such as inorganic salts, optionally in the presence of solvents, such as toluene, xylene, dichlorobenzene or N-methylpyrrolidone.
• the color strength and transparency of the pigment can be influenced by varying the aftertreatment.
• the colorants of the formula (1) are suitable for a wide variety of pigment applications. So they can be used for the production of very real pigmented systems, such as mixtures with other substances, preparations, paints, printing inks, colored paper and colored macromolecular substances. When mixed with other substances e.g. those with inorganic white pigments such as titanium dioxide (rutile) or with cement. Preparations are e.g. Flush pastes with organic liquids or doughs and fine doughs with water, dispersing agents and optionally preservatives.
• paint is e.g.
• Printing inks are to be understood as those for paper, textile and tin printing.
• the macromolecular substances can be of natural origin such as rubber, can be obtained by chemical modification such as acetyl cellulose, cellulose butyrate or viscose or can be produced synthetically such as polymers, polyadducts and polycondensates.
• Thermoplastic materials such as polyvinyl chloride, polyvinyl acetate, polyvinyl propionate, polyolefins, e.g.
• the substances pigmented with the claimed products can be in any form.
• the pigments of the formula (I) are also excellent in waterfastness, oil-fast, acid-fast, lime-fast, alkali-fast, solvent-fast, over-lacquer-fast, over-spray-fast, sublimation-fast, heat-resistant, vulcanization-resistant, very economical and easy to distribute in plastic compositions.
• Example 2 The procedure is as in Example 1, but instead of 1-amino-3- (cyan-N-methylcarbamoylmethylene) isoindoline and p-phenylenediamine isoindoline compounds of the formula and diamines of the formula wherein A and -B- have the meaning given in the following table. Pigments are obtained which, in the paint, give colorations in the shades indicated in column 4 and which have comparable properties.
• Example 2 The procedure is as in Example 1, but instead of 1-imino-3- (cyan-N-methylcarbamoylmethylene) isoindoline, the isoindoline compounds given in column 2 of the table below are reacted with p-phenylenediamine. Pigments are obtained which, in the paint, give colorations in the hues indicated in column 3 and which have comparable properties.
• Example 60 The procedure is as in Example 60, but instead of 1-imino-3- (cyan-N-methylcarbamoylmethylene) isoindoline and p-phenylene diisocyanate, isoindoline compounds of the formula XI and diisocyanates of the formula are used wherein A and B 1 have the meaning given in the following table.
• Example 2 0.5 part of the dye obtained according to Example 1 is tumbled onto 100 parts of polystyrene granules (standard brand). The colored granules are homogenized by extrusion (190 to 195 ° C). Orange-colored extrudates are obtained, the coloring of which has good lightfastness.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)
• Paints Or Removers (AREA)
• Plural Heterocyclic Compounds (AREA)
• Indole Compounds (AREA)

Applications Claiming Priority (2)

Publications (3)

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Family Applications (1)

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• 1985
  • 1985-02-05 DE DE19853503776 patent/DE3503776A1/de not_active Withdrawn
• 1986
  • 1986-01-24 US US06/821,972 patent/US4707548A/en not_active Expired - Lifetime
  • 1986-02-03 DE DE8686101341T patent/DE3666044D1/de not_active Expired
  • 1986-02-03 JP JP61020313A patent/JPH07747B2/ja not_active Expired - Lifetime
  • 1986-02-03 EP EP86101341A patent/EP0190692B1/fr not_active Expired

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